How It Could Have Been
by AudreyF
Summary: What if Jess had said something when he called Rory in the episode Those Are Strings Pinocchio? What if he moved to New Haven with Rory?
1. I Think I May Have Loved You

**All Planned Out**

Disclaimer: I don't own it, don't sue me!

Summary: What if Jess had said something when he called Rory in the episode Those Are Strings Pinocchio?

Rating: PG?

This takes place during the scene where Rory is at Chilton with her mom right after graduating when her cell phone rings. And it's not a pay phone in California he's calling from either.

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Rory and Lorelai were talking outside at Chilton when Rory's cell phone rang. Rory dug around her gradation robes and found her cell phone.

"Hello? … Hello?" Rory asked.

No one answered and she didn't recognize the number on the caller ID. Confused, she hung up.

"A hang up?" Lorelai asked her daughter.

"Yeah," she replied.

"You're getting a lot of those lately," she commented.

As soon as Lorelai spoke, the phone in Rory's hand rang again.

"Hello? … Hello?" Rory asked again.

Rory quickly moved through the crowd and went into the deserted hall inside the school. Confused, her mother waited outside for her.

"Jess, is that you? Jess, I'm pretty sure it's you and I'm pretty sure you've been calling and not saying anything but wanna say something," Rory said into the phone.

"Hello? … You're not going to talk? Fine, I'll talk," Rory continued.

"You didn't handle things right at all. You could've talked to me. You could've told me that you were having trouble in school and weren't going to graduate, and that your dad had been there, but you didn't. And you ended up not taking me to my prom and not coming to my graduation and leaving again without saying goodbye again, and that's fine, I get it, but that's it for me. I'm going to Europe tomorrow and I'm going to Yale and I'm moving on. And I'm not going to pine. I hope you didn't think I was going to pine, okay?" she ranted.

"I think … I think I may have loved you, but I just need to let it go. So, that's it, I guess. Um, I hope you're good. I want you to be good, and, um, okay, so, goodbye. That word sounds really lame and stupid right now, but there it is," she said, about to say goodbye again and hang up.

"I love you too, Rory," Jess finally said.

"What … what did you say?" Rory stammered, shocked that Jess had spoken.

"Rory-" he started again.

"Yeah, me too," she replied, understanding what he had said.

"Look, I'm sorry I kept hanging up on you. I just didn't know what to say," he explained.

"Jess, it's me. You know you can talk to me," Rory pointed out.

"I know, but…" he paused for a moment.

"But what? But you left me and didn't even say a word? But you didn't even leave me with so much as a 'Hey Ror' I'm leaving town'?" she fumed.

"Rory, I don't want to fight. Look, I know you wanted to go to prom and wanted to see me graduate and that you wanted me at your graduation, but my dad was back and it just seemed like a good idea," Jess said.

"You know, I was going to mention you in my speech today," Rory said.

"Why?" Jess asked.

"Because you're my boyfriend. Were, were my boyfriend and because it just seemed to make sense that I talk about you when I talked about my world of books," she explained.

"Huh," muttered Jess.

"Huh! Huh? That's all you have to say?" Rory was still angry.

"Rory, I screwed up okay?" Jess shot back.

"Yeah," she replied.

"I can turn around and leave if that's what you want. Is that what you want?" he asked.

"Huh?" Rory asked, not mimicking Jess, but responding out of confusion.

"Crap," she heard him mumble.

"Jess, where are you?" she asked.

"What's it matter to you where I am? You said yourself we're not together anymore," Jess replied.

"Jess," Rory whined.

"Hey, you okay?" Lorelai asked, walking into the hall.

"I gotta go," she quickly hung up the phone.

"I'm okay," she said to her mom.

"Come on," Lorelai said, leading her down the hall.


	2. I Had It All Planned Out

After leaving the school they went back to Stars Hollow for her graduation party. After a few hours Rory told her mom that she was tired and was going to go home. She insisted that her mom stay and have fun and that she would be fine alone. So Rory headed home in the dark, but as she got closer she took a different turn and headed to the bridge. When she got there, she saw an all too familiar figure sitting there smoking a cigarette in an all too familiar way.

"Jess? What in the world are you doing back here?" she asked, approaching him.

"Nice to see you too," he answered.

"Where were you when you called this afternoon?" she continued, sitting across from him.

"Bus," he replied, putting out the cigarette.

"Why didn't you stay? You know I wouldn't have been mad at you. Okay, maybe a little, but I'd get over it. I just want to know why. What happened? You could have quit your job at Wal-Mart. You didn't really need a second job anyway," Rory rambled.

"You don't need me Rory, your going to Yale this fall. You'll meet a prestigious guy, fall in love and have little Ivy League babies and live happily ever after. I'll be the guy stocking the shelves at the stores you're to rich to go to. You deserve someone else Rory," he spat out.

"Ivy League babies?" Rory looked like she was trying not to laugh.

"Yeah," Jess realized how stupid it sounded too.

"Jess, you know that's not me. Since when have I ever cared about stuff like that? I like Wal-Mart, if you ask nice enough they'll give you a smiley face sticker too," she stated.

"You never answered my questions," she said after a pause.

"The ones about school and the second job?" he asked.

"Yeah," she said in Jess' monosyllabic tone.

"You know I've never liked school. Everyone's so stupid. It's all about the jocks and the popular kids. All it is is a freak show," he said.

"That still doesn't explain the second job. I mean, what could you have possibly needed that cost so much money you and Luke together couldn't afford it?" she asked.

He didn't say anything. He just pulled out a small box and handed it to her.

"What's this?" she stared down at the dark blue box.

"I had it all planned out Rory. I was going to make you proud of me. I was going to graduate and take you to the prom and then I was going to go to your graduation. I had a whole plan for tonight Ror'. I've had it planned for months. I was going to take you out and afterwards I was going to take you to the bridge and tell you that I loved you and then I was going to give that to you. I needed a job so I could afford it. I thought I had it all worked out, but then the principal said I'd skipped too much school to graduate. I was going to school, I wasn't cutting as many classes, I wanted to prove to you I could do it," Jess explained.

Rory was rather shocked at his admission and by the fact that he had said so much.

"What made you think you had to prove yourself to me? I figured you already knew how I felt about you Jess. And I don't care if you have to go back to school and if you go back to school that would prove a lot. Not that you need to prove yourself, I'm just saying that if you had to, which you don't, it would be a very good way," she answered.

"You gonna open it or what?" Jess pointed to the box, not wanting to talk anymore.

"Oh … sure," she said, lifting the lid.

Rory looked at the box's content and back at Jess. She wondered if her assumptions were right. Could Jess really be embarrassed? Or was it nervousness? She wasn't quite sure.

"I know were not together anymore, but I still want you to have it," Jess finally said.

"Was this my graduation present?" she asked.

"No," he said.

"Not that you were supposed to get me a graduation present, but if it's not then what is it for?" Rory questioned.

"It was for when you went off to Yale and I was going to be stuck here in this stupid town. It was supposed to be a promise ring. Don't think I'm turning into some freaking romantic or anything, I just didn't want all those guys at school to think you were available or anything," replied Jess.

"Oh," Rory said, sounding like Jess again.

"I still don't get why you left though," Rory said after a long few moments of silence.

"I don't know Rory. It's just that my dad was back and it seemed like a good opportunity and everything was messed up. So, why not? I figured you'd want to be free to date whoever you wanted to in college, not be stuck with a bad boy here in Stars Hollow repeating the twelfth grade," he said bitterly.

"Huh," she said, sounding more and more like Jess.

"I figured that since no one knew me in California I wouldn't be such a disappointment to everyone, but man you should see what living with dad's like," Jess said.

"What's it like?" Rory asked, breaking from her monosyllabic sentences.

"Their place is okay, my dad is too, but his girlfriend is messed up. I mean she seems okay at first, but she's like the female version of Kirk and her daughter hides in the cupboard all day," Jess stated.

"Sounds like they belong in Stars Hollow more than we do," she laughed.

"Yeah," Jess said, resuming his monosyllabic tendencies.

"Jess," Rory said.

"Huh?" he replied.

"You were right. What you said about me wanting to date whoever I wanted in college, that was true. That whoever was you. You were wrong Jess and I thought you knew me well enough to know that," she admitted.

Jess didn't say anything.

"I still want to be your girlfriend Jess," she said.

"We never broke up in the first place," he pointed out.

"Huh," she mimicked him.

"But you can't do this anymore Jess. You can't just leave me whenever you assume I'm going to do something. Got it?" she said firmly.

He nodded.

"So, now what?" she asked, feeling awkward.

"Come here," he took her hand and led her away from the bridge, taking the box back from her in the process.

"Where are we going?" she asked, following obediently.

"Pretend I never left. Pretend that we just got back from dinner and a movie and that we left the party at Luke's and that we just walked here," he commanded, putting the box I his coat pocket.

"Okay," she said, slightly confused.

He put his arm around her back like he always did and started walking back to the bridge.

"So did you have a good time tonight?" he asked her, hoping she would play along.

She hesitated a moment and then went along with it.

"Oh, yes, but I'm glad we decided to leave the party since mom got out all my baby pictures," she said.

"Sit down Rory, I want to tell you something," he said when they got to the end of the bridge.

"Okay," she sat down with him.

"I know your going off to college and everything, but I still want us to be together," he started, obviously he had this planned.

"I want us to be together too," she replied.

"I love you Rory," he said sincerely.

"I love you too Jess," she said quietly.

"I got a job at Wal-Mart so I could buy you this," he opened the box he had given her earlier.

"Jess-" she started, knowing this is how he wanted the night to have been.

"It's a promise ring. I know it sounds really dumb, but I don't want any guy to get any idea that your available," he explained as if it were the first time he had told her this.

"It's beautiful," she commented as he put the silver ring with her birthstone on it on her right ring finger.

"I hope you're not upset that I didn't graduate. I wasn't slacking off anymore, but I missed too much at the beginning of the year. I'm going to go back though, I'm gonna graduate," he said, not pretending anymore.

"I'm not pretending anymore Rory," he said.

"I know," she said, leaning over to kiss him.

"I'm proud of you Jess," she told him after they kissed.

"I'm proud of you too," he replied.

"Let's go back to my house," she said, standing up.


	3. He Wanted To Hear My Speech

"I want to hear your graduation speech, the one you wrote before I left," he said when they got to her house.

"Okay, it's in my room. Go sit on the couch, I'll be right back," she said, letting him in and heading for her room.

"Okay," he nodded and went into the living room.

To his surprise she came back wearing her cap and gown.

"Though I'd give you the full effect," she explained.

She stood formally in front of him with her speech and cleared her throat.

"Headmaster Charleston, faculty members, fellow students, family and friends, welcome. We never thought this day would come. We prayed for its quick delivery, crossed days off our calendars, counted hours, minutes, and seconds, and now that it's here, I'm sorry it is because it means leaving friends who inspire me and teachers who have been my mentors. So many people who have shaped my life and my fellow students' lives impermeably and forever. I live in two worlds. One is a world of books. I've been a resident of Faulkner's Yoknapatawpha County, hunted the white whale aboard the Pequod, fought alongside Napoleon, sailed a raft with Huck and Jim, committed absurdities with Ignatius J. Reilly, rode a sad train with Anna Karenina, and strolled down Swann's Way. It's a rewarding world, but my second one is by far superior. My second one is populated with characters slightly less eccentric but supremely real, made of flesh and bone, full of love, who are my ultimate inspiration for everything. Richard and Emily Gilmore are kind, decent, unfailingly generous people. They are my twin pillars, without whom, I could not stand. I am proud to be their grandchild. But my ultimate inspiration comes from my best friend, the dazzling woman from whom I received my name and my life's blood, Lorelai Gilmore. My mother never gave me any idea that I couldn't do whatever I wanted to do or be whomever I wanted to be. She filled our house with love and fun and books and music, unflagging in her efforts to give me role models from Jane Austen to Eudora Welty to Patti Smith. As she guided me through these incredible eighteen years, I don't know if she ever realized that the person I most wanted to be was her. Then there is Jess Mariano, he too lives in a world of books. One year ago he joined me in my own world of books. He challenged me to give Hemmingway another try and even endured Ayn Rand for me. This entire year he has been there for me, thank you Jess. To all my family and friends who have helped, challenged and guided me, thank you, I love you all. As we prepare ourselves today to leave let us not forget everyone who has influenced and inspired us here at Chilton. We appreciate you all." Rory recited.

Jess applauded her.

"Thank you," she said shyly.

"Your welcome," he replied, kissing her.

Rory wrapped her arms around his neck and kissed him back.

"Rory! I can't believe you missed it! Right after you left Miss Patty-" Lorelai stopped as soon as she got into the living room.

"Jess. What is he doing here? And why are you in your graduation robes?" Lorelai was very confused.

"Mom! Your back early!" was all Rory said.

"Hi Lorelai," Jess said.

"Hi. Rory, explain please," she said, turning her attention back to her daughter.

"Jess is back and he wanted to hear my speech, so I thought it would be more fun to do it in this. –" she was going to continue but Lorelai cut her off.

"What is that?" Lorelai demanded, pointing to the ring.

"Oh, that. Jess gave it to me," she answered.

"Why?" she asked, now to Jess.

"Oh, gee Miss Gilmore I didn't know I had to get permission from you before I gave anything to Rory," he said sarcastically.

"Mom just sit down and I'll explain. Okay?" Rory said slowly, sitting down on the couch.

"Fine," Lorelai answered, flopping onto the couch.

"Ror' I'm gonna go, I need to talk Luke into letting me crash at his place," Jess said.

"Alright, I'll come over to the diner tomorrow before I go to Europe," she replied.

He nodded and gave her a quick kiss before leaving.

"Start explaining," Lorelai demanded as soon as Jess left.

So Rory told her the whole story. Meanwhile Jess was at the now empty diner having a shouting match with his uncle. After much negotiation, Luke gave in yet again. Lorelai too wasn't very happy, but she decided to just wait and see how everything panned out.


	4. Stop Gawking

The next morning Lorelai and Rory trudged to the diner with all of their luggage.

"Hey Luke," Lorelai said, sitting down at a table.

"Hey," he grunted.

"So I'm assuming Jess came over last night?" Rory asked.

"Yeah," Luke replied.

"Are you gonna let him stay?" Rory questioned.

"For now, it's only temporary. He's got till the end of summer to find a place of his own," he said.

"Oh," Rory answered.

They ate their breakfast and it was almost time to leave.

"I'm going to go up and say goodbye to Jess," Rory said after drinking the last of her coffee.

"Okay. Don't be up too long. Remember what happened the last time I walked in on you two?" Lorelai said.

"Yes I do. I won't be long mom," she answered, heading up the stairs.

When Rory got upstairs Jess was still asleep in his bed. Contemplating how to wake him up she sat down on the edge of the bed.

"Jess," she called.

He was still sleeping, so from where she sat on the bed she started bouncing up and down.

"Geez Luke," Jess started.

"Hi!" Rory chirped when he rolled over and saw her.

"Hey," he replied sleepily.

"That was an interesting way to wake me up," Jess said as he sat up.

"I thought so," Rory replied.

"What are you doing up here?" he asked.

"You don't want me here?" she teased.

"Of course I want you here. I'm just wondering why you actually are here," he said as he stood up and pulled on a pair of jeans.

"I was just … uh," she blushed at the sight of him in only his boxers and lost her train of thought.

"Stop gawking," he said, pulling on his shirt.

"I wasn't gawking," she argued.

"Yes you were," he argued back.

"No-" she was cut off by Jess pulling her up and kissing her.

"Are you trying to shut me up?" she asked.

He didn't reply and he kissed her again.

"Because I think you are," she continued.

He just kissed her again.

"I have to go," Rory finally said.

"Why?" he asked before once again kissing her.

"My mom's waiting," she said breathlessly.

"She can wait longer," Jess murmured between kisses.

"I have a plane to catch," she managed to say.

"Fine," he finally said with a sigh.

"You'll be here when I get back. Won't you?" she asked, stepping back and eyeing him.

"Yes Rory. I promise," he assured her.

"Good. I'll be back in about a month," Rory said happily.

"I'll be here," he mumbled.

"Bye! I love you," she said giving him a quick kiss.

"Love you too," he replied as they walked down to the diner.

"Ready babe?" Lorelai asked when Rory came back.

"Yep, let's go," Rory said, lugging on her backpack.

They said their goodbyes and headed off to Europe. Rory had some doubts as to whether or not Jess would be there for her when she got back though.


	5. Hon, You're Going To Yale Next Month

Finally, the exhausted duo got back to Europe just over one month later. Once they had a good nights sleep and did some laundry the next morning, they headed off to Luke's for some coffee and breakfast. After greeting the townspeople Rory and Lorelai sat down at the diner and Luke took their order.

"Hey Luke, where's Jess?" Rory asked.

"Oh, he moved out about a week ago," Luke responded.

"Really? Where'd he move to?" she asked nervously.

"New Haven," Luke answered.

"New Haven?" Rory echoed.

"Yep. Here, he told me to give this to you," Luke said before leaving to help another customer.

It was a slip of paper with his new address and phone number on it.

"Why on earth would he move to New Haven?" Rory asked her mom.

"I don't know. Maybe to be with you?" Lorelai pointed out the obvious.

"But I'm in Stars Hollow!" she replied, clearly not getting it.

"Hon, you're going to Yale next month! I didn't think you hit your head that hard on the luggage rack coming home," her mother said.

"Oh, right. I guess I just wasn't expecting him to stick around," Rory admitted.

"Ror, if you really want to be with Jess you're going to have to believe in him a little bit more," Lorelai told her daughter.

Rory nodded.

"I'm gonna go," Rory said, standing up.

"Where are you going?" her mother asked.

"To see Jess," she replied.

"Well at least take the Jeep," she said, handing her the keys.

"Thanks mom, I'll be home by tonight," she said as she hugged her.

"Drive safe!" she said as Rory exited the diner.

It took her a while, but she found the apartment and went up to knock on the door. No one answered.

"Are you looking for Jess?" someone asked.

"Yes," Rory answered, turning to the man walking his dog.

"He left for work about 10 minutes ago," he replied.

"Do you know where he works?" she asked.

"Over on 3rd street, at the book store," he told her.

"Thank you," Rory said before turning back to the car.

She made her way over to the small used bookstore and went inside. Rory went up to a worker and asked for Jess. After being told what section he was in she wandered off to find him. She found him in the classics section stocking Mark Twain books.

"Hey," she said softly.

"Rory. How'd you find me," he asked, putting the books down and walking over to her.

"I have my ways," she said.

"I see. Did you have a good trip?" Jess replied.

"Yeah, I'll tell you about it when we have more time," Rory answered.

"Okay. Do you want to go somewhere for lunch?" he asked.

"Sure," she said.

"Meet me at the front of the store an hour and a half and I'll take you someplace," he told her.

"Alright," she responded.

She kissed him and went to go wander around and look at the books. She was sitting in an armchair near the front of the store reading when Jess got off for his lunch break.

"Ready?" he asked her.

"Yep," she said, putting the book in her bag.

"What'd you get?" Jess asked, looking at the bag.

"Hemmingway," she responded casually.

"I don't believe you," he said.

"See for your self," she said, handing him the bag.

"Huh. Rory Gilmore reading Hemmingway voluntarily. What happened in Europe?" he joked.

"Just thought I'd give it another chance," she shrugged.

Once they got to the restaurant Rory proceeded to rant incessantly about her trip to Europe.

"So I'm assuming you enjoyed the trip," he said after hearing a very interesting story about Lorelai attempting to get a mime to talk.

"Mm-hm. So what did you do all this time. I mean, besides move and get a job and stuff," she asked.

"Not much. I did get this though," he answered, pulling out an envelope and handing it to her.

"What's this?" she questioned, taking it.

"Open it," Jess said mysteriously.

"Oh my god! Jess! You got your GED!" she shrieked.

"It's not that big of a deal," he said, glancing at the people who were turning their attention to Rory.

"Yes it is!" she insisted, leaning over the table to give him a kiss.

"I'm very proud of you," she said after sitting back down and giving him the envelope.

"Thanks," he mumbled.

"So how did you have time to do this?" she asked.

"I just registered, paid the fee and took the test. I passed, so I got it," he shrugged.

"You know, at first I was afraid you weren't gonna keep your promise and then when Luke said you moved out I got scared. I know it was stupid of me and I know I should have believed you, but I believe you now, I really do. I'm sorry," she admitted.

"It's okay Rory. I was the one who ran away. Plus, giving me and Hemmingway another chance in the same day, that's pretty impressive," Jess said.

"I thought so," she said with a smirk.

"I took the rest of the day off, you wanna come see my apartment?" he asked after paying the bill.

"Oh, you didn't have to take the day off for me," Rory replied.

"I wanted to. Come on," he insisted.


	6. Jess Wants You To Move In With Him

After following Jess in the Jeep back to his apartment he gave her a tour around his place. It was a small, sparse, bachelor pad, but Rory liked it.

"Impressive," she commented, scanning through his books to see if he had any new ones.

"The books or the apartment?" Jess asked.

"Both," Rory answered.

He nodded and sat down on the couch, inviting Rory to sit next to him.

"So what's going to happen when I start college?" she asked.

"What do you mean? Yale's only ten minutes from here," he noted.

"I know, but are things gonna be different? I mean, how often am I going to see you?" Rory questioned.

"Depends on how much you come by," he answered.

"Well, I hope you'll come by my dorm too. This relationship has to work both ways you know," she joked.

"You could just move in with me if you want to save some money," he offered.

"Move in?" she repeated.

"Yeah," he said.

"Wow. That's a big decision. Are you sure?" Rory asked.

"Yeah. Ror' I know you want to. Think of how many books there'd be if you moved in with me. All of mine and all of yours, there'd be hundreds," he said, trying to entice her.

"Jess," she accused, catching on.

"I'm just saying," he replied.

"I'll think about it. I have to talk to my mom about it first," she said, leaning into Jess.

"Okay," he replied, draping his arm around her and kissing her forehead.

After they watched a movie and took turns reading her new Hemmingway book Rory reluctantly headed back to Stars Hollow.

"Mom!" Rory called as she came in.

"Hey!" Lorelai called from the living room.

"Hey," Rory echoed, coming into the room.

"Have a good time?" her mother asked.

"Yeah, we went out to eat and I got to see where he worked and then I saw his apartment and he offered that I move in with him," she said as casually as possible.

"Move in with him! Jess wants you to move in!" Lorelai repeated in shock.

"What's so bad about that? It would save money on dorm fees and cafeteria fees," she pointed out.

"Well, yeah, but Ror' do you really want to move in with him? Remember, he snores," she said, desperate to convince her daughter otherwise.

"Lot's of people snore," Rory shrugged.

"Are you sure you know what you're getting into? This is a big commitment," she said.

"I know mom. I really want this," she was smiling.

"I can't stop you honey. Just make sure this is really what you want before you agree okay?" Lorelai asked.

"I promise. I'm gonna go to bed now," she hugged her mom and walked to her room.

"Night," Lorelai called.

"Night," Rory called back.


End file.
